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Chem Res Toxicol. 2015 Jun 15;28(6):1209-15. doi: 10.1021/acs.chemrestox.5b00047. Epub 2015 May 21.

4,5-cis unsaturated α-GalCer analogues distinctly lead to CD1d-mediated Th1-biased NKT cell responses.

Author information

1
†Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. China.
2
‡State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, P. R. China.
3
§Institut Parisien de Chimie Moleculaire, UMR CNRS 8232, Universite Pierre et Marie Curie-Paris 6, 75005 Paris, France.
4
∥Institute for Interdisciplinary Research, Jianghan University, Wuhan Economic and Technological Development Zone, Wuhan 430056, P. R. China.

Abstract

The total synthesis of 4,5-cis unsaturated α-GalCer analogues was achieved, and their immune-response altering activity was assessed in vitro as well as in vivo in mice. Using glycosyl iodide as a glycosyl donor, construction of the sphingosine unit was shortened by four steps and single α-stereoselectivity was achieved in good yield (67%). With regard to the therapeutic use of α-GalCer, the novel analogues (1b and 1c) distinctly induced a Th1-biased cytokine response, avoiding induction of a contradictory response and overstimulation.

PMID:
25955524
DOI:
10.1021/acs.chemrestox.5b00047
[Indexed for MEDLINE]

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